There have been many reports concerning selective synthetic methods of primary amines from of old, and examples of known methods include Gabriel reaction (for example, non-Patent Document 1) using phthalimide and related reactions (for example, non-Patent Document 2), Delepine reaction (for example, non-Patent Document 3) using hexamethylenetetramine, and the like. However, all of these methods are not necessarily satisfactory from the industrial point of view because these methods use expensive amination agents and include complicated decomposition operations. On the other hand, methods using inexpensive ammonia as an amination agent are industrially useful. However, these methods have difficulties in suppressing formation of secondary amines and tertiary amines and therefore, primary amines could not be selectively obtained (Patent Document 1). Under these circumstances, a method is known for selective producing a primary amine in the presence of an aromatic aldehyde (Patent Document 2). It is however necessary to recover the aromatic aldehyde separately and therefore, this method is not necessarily satisfactory.
non-Patent Document 1: Angew. Chem. Int. Ed. Engl., (1968), Vol. 7, p 919 (1968)
non-Patent Document 2: Synthesis, 1990, p 122
non-Patent Document 3: Synthesis, 1979, p 161
Patent Document 1: JP 45-34127 B
Patent Document 2: JP 2002-212148 A